The present invention relates to cyclic acetals of 2-methyl-2-pentenal and novel compositions using such cyclic acetals of 2-methyl-2-pentenal to alter, modify, augment or enhance the flavor and/or aroma of foodstuffs, medicinal products, toothpastes, or chewing gum or impart flavor and/or aroma to said foodstuffs, medicinal products, toothpastes or chewing gum.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors to (or in) foodstuffs, medicinal products, toothpastes and/or chewing gum. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Sweet, fruity, gooseberry, green, aniseed, licorice, floral and herbal aroma characteristics and sweet, fruity, gooseberry, green, spearmint, aniseed, licorice, floral, and herbal flavor characteristics with albedo-like flavor nuances are particularly desirable for uses in many foodstuff flavors, chewing gum flavors, toothpaste flavors and medicinal product flavors.
Cyclic acetals of unsaturated aldehydes, wherein the cyclic acetal contains a five membered acetal moiety are known in the prior art. However, the use flavor uses of the cyclic acetals of our invention and one of the cyclic acetals of our invention (wherein R is methyl) have been heretofore unknown.
U.S. Pat. No. 3,760,303 (1971) discloses the cyclic acetal of 2,4-hexadienal with ethylene glycol and discloses its use in the bouquet of citrus-type odorant formulations. This compound has the structure: ##STR2##
Netherlands published application No. 6,406,295 (1965) discloses gamma, delta-unsaturated aldehyde derivatives for use as perfumes, for example in soaps. These derivatives are cyclic acetals and have the structures: ##STR3## wherein R is hydrogen or methyl.
German Offenlegungschrift No. 2,103,567 (1971) discloses the use as perfumes of 2-(1-alkyl-2-alkenyl)-1,3-dioxolanes having the structure: ##STR4##
In the Federal Register 31, 7563 (May 26, 1966) and in Chem. Abstracts 62, 11055e the compound having the structure: ##STR5## is disclosed to be useful as a synthetic food flavoring substance.
Beilstein, Vol. E II19 at page 16:5(2) discloses 2-(1-methyl-1-butenyl)1,3-dioxolane having the structure: ##STR6## The Beilstein Abstract summarizes the article by Hibbert et al. J. Am. Chem. Soc. 51 (1929) page 611 (Title: "Studies on Reactions Relating to Carbohydrates and Polysaccharides. XX. Comparison of Tendencies of Saturated and Unsaturated Aldehydes Toward Cyclic Acetal Formation"). This compound is shown to be prepared by reacting alpha methyl beta ethyl acrolein with ethylene glycol using a 40% sulfuric acid catalyst. The compound is indicated to have a boiling point of 170.degree.-174.degree. C. at 12 mm Hg pressure.
2-(1-ethyl-1-pentenal)-1,3-dioxolane and 2-(1-propenyl)-4-methyl-1,3-dioxolane are shown to be prepared by Heywood and Phillips, J. Org. Chem. 25 (1960) page 1699 entitled: "The Oxidation of Unsaturated Acetals and Acylals With Peracetic Acid".
None of the foregoing references discloses or implies the subject matter of the instant invention.